Synthesis of 3'-Acetamidoadenosine Derivatives as Potential A3 Adenosine Receptor Agonists.

Autor:	Chun, MoonWoo, Choi, SungWook, Kang, TaeKyung, Choi, WonJun, Kim, HeaOk, Gao, Zhan-Guo, Jacobson, KennethA., Jeong, LakShin
Předmět:	ADENOSINES HYDROGEN bonding HYDROBORATION STERIC hindrance CHEMICAL reactions
Zdroj:	Nucleosides, Nucleotides & Nucleic Acids; Apr2008, Vol. 27 Issue 4, p408-420, 13p, 3 Diagrams
Abstrakt:	On the basis of high binding affinity of 3'-aminoadenosine derivatives 2b at the human A3 adenosine receptor (AR), 3'-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A3AR, our results revealed that 3'-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A3AR. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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